Water → HCID 178455362, compound

HRID 1280588Notes

Reaction equation

HRID 1280588 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:19][C:18]2[C:13](=[N:14][C:15]([NH:20][C@H:21]3[CH2:26][CH2:25][C@H:24]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:23][CH2:22]3)=[N:16][CH:17]=2)[NH:12][C:11]1=[O:35].[CH2:36](Br)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.O>CN1CCCC1=O>[CH2:36]([N:12]1[C:13]2=[N:14][C:15]([NH:20][C@H:21]3[CH2:22][CH2:23][C@H:24]([O:27][Si:28]([C:31]([CH3:32])([CH3:34])[CH3:33])([CH3:29])[CH3:30])[CH2:25][CH2:26]3)=[N:16][CH:17]=[C:18]2[CH2:19][N:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[Cl:3])[C:11]1=[O:35])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178455363HCID 178455363, compound

Product 1

HCID 178455362HCID 178455362, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Sodium hydride (44 mg, 1.1 mmol (60% oil dispersion)) was added to a suspension of 3-(2-chlorophenyl)-7-(trans-4-tert-butyldimethylsilyloxycyclohexyl-amino)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (486 mg, 1 mmol) in 1-methyl-2-pyrrolidinone, and was stirred at room temperature for 25 minutes. To this solution was added benzyl bromide (0.12 mL 1 mmol) and stirred at room temperature for 4 hours. The reaction mixture was added to water and extracted with ethyl acetate. The layers were separated, and the organic layer was washed with water, dried with magnesium sulfate, concentrated in vacuo. The residue was purified by column chromatography using 25:75 acetone/hexane as eluant to give 1-benzyl-3-(2-chlorophenyl)-7-(trans4-tert-butyldimethylsilyloxycyclohexylamino)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one as an oil.

Workup

  1. stirringstirred at room temperature for 4 hours
  2. extractionextracted with ethyl acetate
  3. customThe layers were separated
  4. washthe organic layer was washed with water
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-09700a71131242ca8c4536c99f285d24
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

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